Showing metabocard for Allysine (BMDB0001263)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:16 UTC
Update Date2020-05-19 22:01:07 UTC
BMDB IDBMDB0001263
Secondary Accession Numbers
  • BMDB01263
Metabolite Identification
Common NameAllysine
DescriptionAllysine, also known as 6-oxonorleucine or alpha-aasa, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Allysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. Allysine participates in a number of enzymatic reactions, within cattle. In particular, Allysine and L-glutamic acid can be biosynthesized from saccharopine through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Allysine can be converted into aminoadipic acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In cattle, allysine is involved in the metabolic pathway called the lysine degradation pathway. Allysine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-5-formylvaleric acidChEBI
2-Aminoadipate 6-semialdehydeChEBI
6-OxonorleucineChEBI
alpha-Aminoadipic acid delta-semialdehydeChEBI
alpha-Aminoadipic delta-semialdehydeChEBI
HCO-[CH2]3-CH(NH2)-COOHChEBI
2-Amino-5-formylvalerateGenerator
2-Aminoadipic acid 6-semialdehydeGenerator
a-Aminoadipate delta-semialdehydeGenerator
a-Aminoadipic acid delta-semialdehydeGenerator
alpha-Aminoadipate delta-semialdehydeGenerator
Α-aminoadipate δ-semialdehydeGenerator
Α-aminoadipic acid δ-semialdehydeGenerator
a-Aminoadipic delta-semialdehydeGenerator
Α-aminoadipic δ-semialdehydeGenerator
a-Aminoadipate δ-semialdehydeGenerator, HMDB
a-Aminoadipic acid δ-semialdehydeGenerator, HMDB
a-Aminoadipic δ-semialdehydeGenerator, HMDB
(2S)-2-amino-6-OxohexanoateHMDB
(2S)-2-amino-6-Oxohexanoic acidHMDB
2-amino-HexanedioateHMDB
2-amino-Hexanedioic acidHMDB
2-amino-Hexanedioic acid semialdhydeHMDB
2-Aminoadipate semialdehydeHMDB
2-Aminoadipate-6-semialdehydeHMDB
5-Formyl-norvalineHMDB
6-oxo-L-NorleucineHMDB
6-oxo-NorleucineHMDB
alpha-Aminoadipic semialdehydeHMDB
L-2-Aminoadipate 6-semialdehydeHMDB
L-6-OxonorleucineHMDB
L-AllysineHMDB
2-Aminoadipic semialdehydeMeSH, HMDB
alpha-AASAMeSH, HMDB
alpha-Aminoadipate semialdehydeMeSH, HMDB
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name2-amino-6-oxohexanoic acid
Traditional Nameallysine
CAS Registry Number1962-83-0
SMILES
NC(CCCC=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)
InChI KeyGFXYTQPNNXGICT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.9ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)2.25ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.96 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0303320
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022519
KNApSAcK IDC00051877
Chemspider ID202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17027
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

Enzyme Details
1. Alpha-aminoadipic semialdehyde synthase, mitochondrial
General function:
Amino acid transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-oxoglutarate reductase and saccharopine dehydrogenase activity, respectively (By similarity).
Gene Name:
AASS
Uniprot ID:
A8E657
Molecular weight:
102084.0
Reactions
Saccharopine + Water + NAD → Allysine + L-Glutamic acid + NADHdetails
Enzyme Details
2. Saccharopine dehydrogenase-like oxidoreductase
General function:
Involved in binding
Specific function:
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NAD(+) + H(2)O = L-glutamate + 2-aminoadipate 6-semialdehyde + NADH
Gene Name:
SCCPDH
Uniprot ID:
Q3T067
Molecular weight:
47320.0
Enzyme Details
3. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Energy production and conversion
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism (By similarity).
Gene Name:
ALDH7A1
Uniprot ID:
Q2KJC9
Molecular weight:
58582.0
Reactions
Allysine + NAD + Water → Aminoadipic acid + NADHdetails